U.S. patent number 10,870,614 [Application Number 16/797,690] was granted by the patent office on 2020-12-22 for processes for producing trifluoroiodomethane using metal trifluoroacetates.
This patent grant is currently assigned to Honeywell International Inc.. The grantee listed for this patent is Honeywell International Inc.. Invention is credited to Christian Jungong, Haiyou Wang, Terris Yang.
United States Patent |
10,870,614 |
Jungong , et al. |
December 22, 2020 |
Processes for producing trifluoroiodomethane using metal
trifluoroacetates
Abstract
The present disclosure provides a process for producing
trifluoroiodomethane. The process includes providing a metal
trifluoroacetate, iodine monochloride, and a solvent, and reacting
the metal trifluoroacetate and iodine monochloride in the presence
of the solvent to produce trifluoroiodomethane.
Inventors: |
Jungong; Christian (Depew,
NY), Wang; Haiyou (Amherst, NY), Yang; Terris (East
Amherst, NY) |
Applicant: |
Name |
City |
State |
Country |
Type |
Honeywell International Inc. |
Morris Plains |
NJ |
US |
|
|
Assignee: |
Honeywell International Inc.
(Charlotte, NC)
|
Family
ID: |
1000005256281 |
Appl.
No.: |
16/797,690 |
Filed: |
February 21, 2020 |
Prior Publication Data
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Document
Identifier |
Publication Date |
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US 20200283361 A1 |
Sep 10, 2020 |
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Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
Issue Date |
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62813503 |
Mar 4, 2019 |
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Current U.S.
Class: |
1/1 |
Current CPC
Class: |
C07C
17/363 (20130101); C07C 19/16 (20130101); C07C
17/093 (20130101) |
Current International
Class: |
C07C
17/363 (20060101); C07C 19/16 (20060101); C07C
17/093 (20060101) |
References Cited
[Referenced By]
U.S. Patent Documents
Foreign Patent Documents
Other References
International Search Report and Written Opinion received for PCT
Patent Application No. PCT/US2020/020598, dated Jun. 23, 2020, 12
pages. cited by applicant .
Song et al., "Fluoroalkylation reactions in aqueous media: a
review", Green Chemistry, vol. 20, Feb. 8, 2018, pp. 1662-1731.
cited by applicant.
|
Primary Examiner: Parsa; Jafar F
Attorney, Agent or Firm: Faegre Drinker Biddle & Reath
LLP
Parent Case Text
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is a U.S. Nonprovisional Application which claims
priority to Provisional Application No. 62/813,503, filed Mar. 4,
2019, which is incorporated herein by reference in its entirety.
Claims
What is claimed is:
1. A process for producing trifluoroiodomethane (CF.sub.3I), the
process comprising: providing a metal trifluoroacetate, iodine
monochloride, and a solvent; and reacting the metal
trifluoroacetate and iodine monochloride in the presence of the
solvent to produce trifluoroiodomethane.
2. The process of claim 1, wherein in the providing step, a mole
ratio of the metal trifluoroacetate to the iodine monochloride is
from about 0.1:1 to about 2.0:1.
3. The process of claim 1, wherein in the providing step, the metal
trifluoroacetate is at least one selected from the group of lithium
trifluoroacetate, potassium trifluoroacetate, sodium
trifluoroacetate, rubidium trifluoroacetate, cesium
trifluoroacetate, calcium trifluoroacetate, magnesium
trifluoroacetate, iron trifluoroacetate, zinc trifluoroacetate, and
copper trifluoroacetate.
4. The process of claim 1, wherein in the providing step, the
solvent comprises less than about 500 ppm by volume of water.
5. The process of claim 1, wherein in the providing step, the
solvent is at least one selected from the group of an ionic liquid
and a polar aprotic solvent.
6. The process of claim 5, wherein the solvent is at least one
selected from the group of imidazolium salts, caprolactamium
hydrogen sulfate, sulfolane, N,N-dimethylacetamide, and dimethyl
sulfone.
7. The process of claim 6, wherein the solvent consists of
sulfolane.
8. The process of claim 1, wherein reacting the metal
trifluoroacetate and iodine monochloride is further in the presence
of a catalyst.
9. The process of claim 8, wherein the catalyst includes at least
one selected from the group of copper (I) iodide, ferrous chloride,
and zinc (II) iodide.
10. The process of claim 1, wherein in the reacting step, the metal
trifluoroacetate, the iodine monochloride, and the solvent are at a
temperature from about 100.degree. C. to about 250.degree. C.
11. A process for producing trifluoroiodomethane (CF.sub.3I), the
process comprising: mixing a metal trifluoroacetate, iodine
monochloride, and a solvent; and heating the metal
trifluoroacetate, iodine monochloride, and the solvent to react the
metal trifluoroacetate and iodine monochloride to produce
trifluoroiodomethane and a metal chloride.
12. The process of claim 11, further including separating the
trifluoroiodomethane from the metal chloride.
13. The process of claim 11, wherein the process is a continuous
process.
14. The process of claim 11, wherein the process is a batch
process.
15. The process of claim 11, wherein the metal trifluoroacetate is
at least one selected from the group of lithium trifluoroacetate,
potassium trifluoroacetate, sodium trifluoroacetate, rubidium
trifluoroacetate, cesium trifluoroacetate, calcium
trifluoroacetate, magnesium trifluoroacetate, iron
trifluoroacetate, zinc trifluoroacetate, and copper
trifluoroacetate.
16. The process of claim 11, wherein the solvent is at least one
selected from the group of an ionic liquid and a polar aprotic
solvent.
17. The process of claim 16, wherein the solvent is at least one
selected from the group of imidazolium salts, caprolactamium
hydrogen sulfate, sulfolane, N,N-dimethylacetamide, and dimethyl
sulfone.
18. The process of claim 11, wherein the metal trifluoroacetate and
iodine monochloride react in the presence of a catalyst.
19. The process of claim 18, wherein the catalyst includes at least
one selected from the group of copper (I) iodide, ferrous chloride,
and zinc (II) iodide.
20. The process of claim 11, wherein the metal trifluoroacetate,
the iodine monochloride, and the solvent are heated to a
temperature from about 100.degree. C. to about 250.degree. C.
Description
FIELD
The present disclosure relates to processes for producing
trifluoroiodomethane (CF.sub.3I). Specifically, the present
disclosure relates to methods to produce trifluoroiodomethane from
metal trifluoroacetates.
BACKGROUND
Trifluoroiodomethane (CF.sub.3I) is a useful compound in commercial
applications, as a refrigerant or a fire suppression agent, for
example. Trifluoroiodomethane is an environmentally acceptable
compound with a low global warming potential and low ozone
depletion potential. Trifluoroiodomethane can replace more
environmentally damaging materials.
Methods of preparing trifluoroiodomethane from metal
trifluoroacetates and elemental iodine are known. For example,
CN102992943B discloses a reaction of sodium trifluoroacetate and
elemental iodine to produce trifluoroiodomethane, carbon dioxide,
and metal iodide. Stoichiometrically, half of the iodine from the
elemental iodide is converted to the metal iodide byproduct instead
of the desired trifluoroiodomethane.
Iodine is one of the most expensive reactants used in the process
of making trifluoroiodomethane from metal trifluoroacetates. Thus,
there is a need to develop a process that more efficiently uses
iodine in the production of trifluoroiodomethane from metal
trifluoroacetates.
SUMMARY
The present disclosure provides processes for producing
trifluoroiodomethane by reacting a metal trifluoroacetate with
iodine monochloride.
In one embodiment, the present invention provides a process for
producing trifluoroiodomethane. The process includes providing a
metal trifluoroacetate, iodine monochloride, and a solvent, and
reacting the metal trifluoroacetate and iodine monochloride in the
presence of the solvent to produce trifluoroiodomethane.
In another embodiment, the present invention provides a process for
producing trifluoroiodomethane. The process includes mixing a metal
trifluoroacetate, iodine monochloride, and a solvent; and heating
the metal trifluoroacetate, iodine monochloride, and the solvent to
react the metal trifluoroacetate and iodine monochloride to produce
trifluoroiodomethane and a metal chloride.
The above mentioned and other features of the disclosure, and the
manner of attaining them, will become more apparent and will be
better understood by reference to the following description of
embodiments taken in conjunction with the accompanying
drawings.
DETAILED DESCRIPTION
The present disclosure provides a liquid phase process for the
manufacture of trifluoroiodomethane (CF.sub.3I) from a metal
trifluoroacetate (CF.sub.3COOM) and iodine monochloride (ICI)
reactants by decarboxylative iodination according to Equation 1
below: CF.sub.3COOM+ICI.fwdarw.CF.sub.3I+CO.sub.2+MCI Eq. 1: where
M may be an alkali metal, such as lithium, potassium, sodium,
rubidium, or cesium; an alkaline earth metal, such as calcium or
magnesium; or a transition metal, such as iron, zinc, or copper.
Thus, the metal trifluoroacetate may include lithium
trifluoroacetate, potassium trifluoroacetate, sodium
trifluoroacetate, rubidium trifluoroacetate, cesium
trifluoroacetate, calcium trifluoroacetate, magnesium
trifluoroacetate, iron trifluoroacetate, zinc trifluoroacetate,
copper trifluoroacetate, or combinations, thereof. As shown in
Equation 1, there is no inherent chemical limitation in the process
chemistry for the near complete conversion of the iodine in the
iodine monochloride to trifluoroiodomethane.
In addition to improved iodine utilization, the use of iodine
monochloride provides other advantages in the production of
trifluoroiodomethane. Iodine monochloride is highly polar due to
the difference in electronegativity and size between the chlorine
and iodine atoms, which makes the chlorine-iodine bond highly
polarizable with the iodine atom having a partial positive
character and the chlorine atom a partial negative character. The
positive character of the iodine atom makes iodine monochloride a
positive iodine source. That is, the iodine is available as a
positively charged ion. Positive iodine is necessary for the
formation of trifluoroiodomethane, based on the reaction of
Equation 1. The highly polar nature of the chlorine-iodine bond
increases its reactivity relative to that of the iodine-iodine
bond. Thus, iodine monochloride is more reactive when compared to
elemental iodine. The availability of the iodine exclusively as
positive iodine may improve the yield of trifluoroiodomethane.
Additionally, iodine monochloride also has a lower melting point
(27.degree. C.) than elemental iodine (113.7.degree. C.) which
makes it relatively easier to process and may result in significant
energy savings. The metal chloride produced in the reaction may be
significantly less corrosive and safer than reaction products
produced in processes using elemental iodine.
The metal trifluoroacetate and the iodine monochloride are
anhydrous. It is preferred that there be as little water in the
reaction as possible because any water in the reaction may favor
secondary reaction pathways resulting in the formation of undesired
byproducts, such as trifluoromethane (CF.sub.3H). Additionally,
iodine monochloride reacts with water to form hydrogen chloride,
hydrogen iodide and oxygen. Besides formation of undesired
byproducts, presence of water will also result in the decomposition
of iodine monochloride, reducing the amount available for reaction
with a direct impact being a reduced productivity, based on the
reaction of Equation 2 below:
ICI+H.sub.2O.fwdarw.HCl+HI+1/2O.sub.2. Eq. 2:
The reaction is carried out in a solvent. Solvents useful for
carrying out the reaction in the liquid phase include
dimethylformamide, dimethyl sulfoxide, ionic liquids, polar aprotic
solvents, or combinations thereof. Examples of ionic liquids
include imidazolium salts and caprolactamium hydrogen sulfate.
Examples of polar aprotic solvents with high boiling points include
sulfolane, N,N-dimethylacetamide, and dimethyl sulfone.
The solvent is substantially free of water. Substantially free of
water means that the amount of water in the solvent is less than
about 500 parts per million (ppm), about 300 ppm, about 200 ppm,
about 100 ppm, about 50 ppm, about 30 ppm, about 20 ppm, or about
10 ppm, or less than any value defined between any two of the
foregoing values. The foregoing ppm values are by weight of the
solvent and any water. Preferably, the amount of water in the
solvent is less than about 100 ppm. More preferably, the amount of
water in the solvent is less than about 50 ppm. Most preferably,
the amount of water in the solvent is less than about 10 ppm.
Metal trifluoroacetates are readily available in commercial
quantities. For example, sodium trifluoroacetate and iodine
monochloride may be obtained from Sigma-Aldrich Corp., St. Louis,
Mo. The solvents may also be readily obtained in commercial
quantities. For example, sulfolane may be also be obtained from
Sigma-Aldrich Corp., St. Louis, Mo.
The reactants may be provided for the reaction at a mole ratio of
metal trifluoroacetate to iodine monochloride as low as about 0.1,
about 0.2, about 0.3, about 0.4, about 0.5, about 0.6, about 0.7,
about 0.8, about 0.9, about 0.95, about 0.99, or about 1, or as
high as about 1.01, about 1.05 about, 1.1, about 1.2, about 1.3,
about 1.4, about 1.5, about 1.6, about 1.8, or about 2.0, or within
any range defined between any two of the foregoing values, such as
about 0.1 to about 2.0, about 0.5 to about 1.5, about 0.6 to about
1.4, about 0.7 to about 1.3, about 0.8 to about 1.2, about 0.9 to
about 1.1, about 0.95 to about 1.05, about 0.99 to about 1.01,
about 1 to about 2, about 0.8 to about 1.5, or about 0.95 to about
1.2, for example. Preferably, the mole ratio of metal
trifluoroacetate to iodine monochloride may be from about 0.8 to
about 1.5. More preferably, the mole ratio of metal
trifluoroacetate to iodine monochloride may be from about 1 to
about 1.2. Most preferably, the mole ratio of metal
trifluoroacetate to iodine monochloride may be about 1.
The reaction may be conducted at a temperature as low as about
100.degree. C., about 110.degree. C., about 120.degree. C., about
130.degree. C., about 140.degree. C., about 150.degree. C., about
160.degree. C., or about 170.degree. C., or at a temperature as
high as about 180.degree. C., about 190.degree. C., about
200.degree. C., about 210.degree. C., about 220.degree. C., about
230.degree. C., about 240.degree. C., or about 250.degree. C., or
within any range defined between any two of the foregoing values,
such as about 100.degree. C. to about 250.degree. C., about
110.degree. C. to about 240.degree. C., about 120.degree. C. to
about 230.degree. C., about 130.degree. C. to about 220.degree. C.,
about 140.degree. C. to about 210.degree. C., about 150.degree. C.
to about 200.degree. C., about 160.degree. C. to about 190.degree.
C., about 170.degree. C. to about 180.degree. C., about 120.degree.
C. to about 130.degree. C., about 110.degree. C. to about
180.degree. C., or about 120.degree. C. to about 250.degree. C.,
for example. Preferably, the reactants are heated to a temperature
from about 110.degree. C. to about 250.degree. C. More preferably,
the reactants are heated to a temperature from about 120.degree. C.
to about 180.degree. C. Most preferably, the reactants are heated
to a temperature of about 175.degree. C.
Pressure is not critical. Convenient operating pressures may range
from about 10 KPa to about 4,000 KPa, and preferably around ambient
pressure, or about 100 KPa to about 250 KPa.
The reaction may be carried out in the presence of, or in the
absence of, a catalyst. The catalyst may be a metal catalyst, such
as copper (I) iodide, ferrous chloride, or zinc (II) iodide, for
example. The catalyst may be a phase transfer catalyst. The phase
transfer catalysts may be selected from the group of quaternary
ammonium salts and quaternary phosphonium salts. A non-limiting
example of a quaternary ammonium salt is tetramethylammonium
chloride (TMAC), while a non-limiting example of a quaternary
phosphonium salt is tetraphenylphosphonium bromide (TPPB).
The reaction is carried out in a liquid phase reactor. The liquid
phase reactor may be a semi-batch or continuously stirred tank
reactor (CSTR). The reaction may be carried out as a batch process
or as a continuous process.
The volatile products of the reaction, including the
trifluoroiodomethane, may be condensed and collected, thus
separating the trifluoroiodomethane from the non-volatile metal
chloride byproduct.
The composition of the volatile organic products of the reaction
may be measured by gas chromatography (GC) and gas
chromatography-mass spectroscopy (GC-MS) analyses. Graph areas
provided by the GC analysis for each of the volatile organic
compounds may be combined to provide a GC area percentage (GC area
%) of the total volatile organic compounds for each of the volatile
organic compounds as a measurement of the relative concentrations
of the volatile organic compounds produced in the reaction.
While this invention has been described as relative to exemplary
designs, the present invention may be further modified within the
spirit and scope of this disclosure. Further, this application is
intended to cover such departures from the present disclosure as
come within known or customary practice in the art to which this
invention pertains.
As used herein, the phrase "within any range defined between any
two of the foregoing values" literally means that any range may be
selected from any two of the values listed prior to such phrase
regardless of whether the values are in the lower part of the
listing or in the higher part of the listing. For example, a pair
of values may be selected from two lower values, two higher values,
or a lower value and a higher value.
EXAMPLES
Example 1
Comparative Manufacture of CF.sub.3I from a Metal Trifluoroacetate
and Elemental Iodine
In this Example, the manufacture of trifluoroiodomethane from
sodium trifluoroacetate (CF.sub.3COONa) and elemental iodine is
demonstrated for comparison purposes. Sodium trifluoroacetate in an
amount of 20 g and elemental iodine in an amount of 38 g were added
to a 300 mL reactor from Parr Instrument Company, Moline, Ill. The
reactor was equipped with a condenser. The reactor was pressure
tested to 300 psig, and then evacuated. Sulfolane in an amount of
60 mL was added to the reactor to form a reactant mixture having a
mole ratio of sodium trifluoroacetate to elemental iodine of about
0.98:1. The reactants and the solvent were obtained from
Sigma-Aldrich Corp., St. Louis, Mo. and used without further
purification.
The reactant mixture was heated to about 175.degree. C. No catalyst
was used in the reaction. Volatile gaseous products and byproducts
were produced as the reaction proceeded. The volatile gases exiting
the condenser were collected in a product collection cylinder
cooled in dry ice.
The composition of the organic compounds in the volatile gases
collected in the product collection cylinder was measured by gas
chromatography (GC). Graph areas provided by the GC analysis for
each of the organic compounds were combined to provide a GC area
percentage (GC area %) of the total organic compounds for each of
the organic compounds as a measurement of the relative
concentrations of the organic compounds. The results are shown in
the Table below.
Example 2
Manufacture of CF.sub.3I from a Metal Trifluoroacetate and Iodine
Monochloride
In this Example, the manufacture of trifluoroiodomethane from
sodium trifluoroacetate (CF.sub.3COONa) and iodine monochloride
(ICI) according to Equation 1 described above is demonstrated.
Sodium trifluoroacetate in an amount of 20 g was added to a 300 mL
reactor from Parr Instrument Company, Moline, Ill. The reactor was
equipped with a condenser. The reactor was pressure tested to 300
psig, and then evacuated. Iodine monochloride in an amount of 25 g
and 60 mL of sulfolane were added to the reactor to form a reactant
mixture having a mole ratio of sodium trifluoroacetate to iodine
monochloride of about 0.95:1. The reactants and the solvent were
obtained from Sigma-Aldrich Corp., St. Louis, Mo. and used without
further purification.
The reactant mixture was heated to about 175.degree. C. No catalyst
was used in the reaction. Volatile gaseous products and byproducts
were produced as the reaction proceeded. The volatile gases exiting
the condenser were collected in a product collection cylinder
cooled in dry ice.
The composition of the organic compounds in the volatile gases
collected in the product collection cylinder was measured by gas
chromatography (GC). Graph areas provided by the GC analysis for
each of the organic compounds were combined to provide a GC area
percentage (GC area %) of the total organic compounds for each of
the organic compounds as a measurement of the relative
concentrations of the organic compounds. The results are shown in
the Table below.
As shown in the Table below, the use of iodine monochloride results
in higher selectivity for trifluoroiodomethane with reduced
production of other byproducts when compared to the use of
elemental iodine.
TABLE-US-00001 TABLE Source of Iodine CF.sub.3I (GC area %) Other
(GC area %) Iodine Monochloride (ICI) 74.58% 25.42% Elemental
Iodine (I.sub.2) 51.61% 48.39%
ASPECTS
Aspect 1 is a process for producing trifluoroiodomethane
(CF.sub.3I), the process comprising providing a metal
trifluoroacetate, iodine monochloride, and a solvent; and reacting
the metal trifluoroacetate and iodine monochloride in the presence
of the solvent to produce trifluoroiodomethane.
Aspect 2 is the process of Aspect 1, wherein in the providing step,
a mole ratio of the metal trifluoroacetate to the iodine
monochloride is from about 0.1:1 to about 2.0:1.
Aspect 3 is the process of Aspect 1, wherein in the providing step,
a mole ratio of the metal trifluoroacetate to the iodine source is
from about 0.8:1 to about 1.5:1.
Aspect 4 is the process of Aspect 1, wherein in the providing step,
a mole ratio of the metal trifluoroacetate to the iodine source is
from about 1.1:1 to about 1.2:1.
Aspect 5 is the process of Aspect 1, wherein in the providing step,
a mole ratio of the metal trifluoroacetate to the iodine source is
about 1:1.
Aspect 6 is the process of any of Aspects 1-5, wherein in the
providing step, the metal trifluoroacetate is at least one selected
from the group of lithium trifluoroacetate, potassium
trifluoroacetate, sodium trifluoroacetate, rubidium
trifluoroacetate, cesium trifluoroacetate, calcium
trifluoroacetate, magnesium trifluoroacetate, iron
trifluoroacetate, zinc trifluoroacetate, and copper
trifluoroacetate.
Aspect 7 is the process of any of Aspects 1-5, wherein in the
providing step, the metal trifluoroacetate is at least one selected
from the group of potassium trifluoroacetate and sodium
trifluoroacetate.
Aspect 8 is the process of any of Aspects 1-5, wherein in the
providing step, the metal trifluoroacetate consists of sodium
trifluoroacetate.
Aspect 9 is the process of any of Aspects 1-8, wherein in the
providing step, the organic solvent comprises less than about 500
ppm by volume of water.
Aspect 10 is the process any of Aspects 1-8, wherein in the
providing step, the organic solvent comprises less than about 100
ppm by volume of water.
Aspect 11 is the process any of Aspects 1-8, wherein in the
providing step, the solvent comprises less than about 50 ppm by
volume of water.
Aspect 12 is the process any of Aspects 1-8, wherein in the
providing step, the comprises less than about 10 ppm by volume of
water.
Aspect 13 is the process of any of Aspects 1-12, wherein in the
providing step, the solvent is at least one selected from the group
of an ionic liquid and a polar aprotic solvent.
Aspect 14 is the process Aspect 13, wherein solvent is at least one
selected from the group of imidazolium salts, caprolactamium
hydrogen sulfate, sulfolane, N,N-dimethylacetamide, and dimethyl
sulfone.
Aspect 15 is the process of Aspect 14, wherein the solvent consists
of sulfolane.
Aspect 16 is the process of any of Aspects 1-15, wherein reacting
the metal trifluoroacetate and iodine monochloride is further in
the presence of a catalyst.
Aspect 17 is the process of Aspect 16, wherein the catalyst
includes at least one selected from the group of copper (I) iodide,
ferrous chloride, and zinc (II) iodide.
Aspect 18 is the process of Aspect 17, wherein the catalyst
consists of copper (I) iodide.
Aspect 19 is the process of Aspect 17, wherein the catalyst
consists of ferrous chloride.
Aspect 20 is the process of Aspect 17, wherein the catalyst
consists of zinc (II) iodide.
Aspect 21 is the process of any of Aspects 1-20, wherein in the
reacting step, the metal trifluoroacetate, the iodine monochloride,
and the solvent are at a temperature from about 100.degree. C. to
about 250.degree. C.
Aspect 22 is the process of any of Aspects 1-20, wherein in the
reacting step, the metal trifluoroacetate, the iodine monochloride,
and the solvent are at a temperature from about 110.degree. C. to
about 250.degree. C.
Aspect 23 is the process of any of Aspects 1-20, wherein in the
reacting step, the metal trifluoroacetate, the iodine monochloride,
and the solvent are at a temperature from about 120.degree. C. to
about 180.degree. C.
Aspect 24 is the process of any of Aspects 1-20, wherein in the
reacting step, the metal trifluoroacetate, the iodine monochloride,
and the solvent are at a temperature from about 170.degree. C. to
about 180.degree. C.
Aspect 25 is a process for producing trifluoroiodomethane
(CF.sub.3I), the process comprising mixing a metal
trifluoroacetate, iodine monochloride, and a solvent; and heating
the metal trifluoroacetate, iodine monochloride, and the solvent to
react the metal trifluoroacetate and iodine monochloride to produce
trifluoroiodomethane and a metal chloride.
Aspect 26 is the process of Aspect 25, further including separating
the trifluoroiodomethane from the metal chloride.
Aspect 27 is the process of either of Aspects 25 or 26, wherein the
process is a continuous process.
Aspect 28 is the process of either of Aspects 25 or 26, wherein the
process is a batch process.
Aspect 29 is the process of any of Aspects 25-28, wherein the metal
trifluoroacetate is at least one selected from the group of lithium
trifluoroacetate, potassium trifluoroacetate, sodium
trifluoroacetate, rubidium trifluoroacetate, cesium
trifluoroacetate, calcium trifluoroacetate, magnesium
trifluoroacetate, iron trifluoroacetate, zinc trifluoroacetate, and
copper trifluoroacetate.
Aspect 30 is the process of any of Aspects 25-29, wherein a mole
ratio of the metal trifluoroacetate to the iodine monochloride is
from about 0.1:1 to about 2.0:1.
Aspect 31 is the process of any of Aspects 25-29, wherein a mole
ratio of the metal trifluoroacetate to the iodine source is from
about 0.8:1 to about 1.5:1.
Aspect 32 is the process of any of Aspects 25-29, wherein a mole
ratio of the metal trifluoroacetate to the iodine source is from
about 1.1:1 to about 1.2:1.
Aspect 33 is the process of any of Aspects 25-29, wherein a mole
ratio of the metal trifluoroacetate to the iodine source is about
1:1.
Aspect 34 is the process of any of Aspects 25-33, wherein the metal
trifluoroacetate is at least one selected from the group of lithium
trifluoroacetate, potassium trifluoroacetate, sodium
trifluoroacetate, rubidium trifluoroacetate, cesium
trifluoroacetate, calcium trifluoroacetate, magnesium
trifluoroacetate, iron trifluoroacetate, zinc trifluoroacetate, and
copper trifluoroacetate.
Aspect 35 is the process of any of Aspects 25-33, wherein the metal
trifluoroacetate is at least one selected from the group of
potassium trifluoroacetate and sodium trifluoroacetate.
Aspect 36 is the process of any of Aspects 25-33, wherein the metal
trifluoroacetate consists of sodium trifluoroacetate.
Aspect 37 is the process of any of Aspects 25-36, wherein the
organic solvent comprises less than about 500 ppm by volume of
water.
Aspect 38 is the process any of Aspects 25-36, wherein the organic
solvent comprises less than about 100 ppm by volume of water.
Aspect 39 is the process any of Aspects 25-36, wherein the solvent
comprises less than about 50 ppm by volume of water.
Aspect 40 is the process any of Aspects 25-36, wherein the
comprises less than about 10 ppm by volume of water.
Aspect 41 is the process of any of Aspects 25-40, wherein the
solvent is at least one selected from the group of an ionic liquid
and a polar aprotic solvent.
Aspect 42 is the process Aspect 41, wherein solvent is at least one
selected from the group of imidazolium salts, caprolactamium
hydrogen sulfate, sulfolane, N,N-dimethylacetamide, and dimethyl
sulfone.
Aspect 43 is the process of Aspect 42, wherein the solvent consists
of sulfolane.
Aspect 44 is the process of any of Aspects 25-43, wherein the metal
trifluoroacetate and iodine monochloride react in the presence of a
catalyst.
Aspect 45 is the process of Aspect 44, wherein the catalyst
includes at least one selected from the group of copper (I) iodide,
ferrous chloride, and zinc (II) iodide.
Aspect 46 is the process of Aspect 45, wherein the catalyst
consists of copper (I) iodide.
Aspect 47 is the process of Aspect 45, wherein the catalyst
consists of ferrous chloride.
Aspect 48 is the process of Aspect 45, wherein the catalyst
consists of zinc (II) iodide.
Aspect 49 is the process of any of Aspects 25-48, wherein the metal
trifluoroacetate, the iodine monochloride, and the solvent are
heated to a temperature from about 100.degree. C. to about
250.degree. C.
Aspect 50 is the process of any of Aspects 25-48, wherein the metal
trifluoroacetate, the iodine monochloride, and the solvent are
heated to a temperature from about 110.degree. C. to about
250.degree. C.
Aspect 51 is the process of any of Aspects 25-48, wherein the metal
trifluoroacetate, the iodine monochloride, and the solvent are
heated to a temperature from about 120.degree. C. to about
180.degree. C.
Aspect 52 is the process of any of Aspects 25-48, wherein the metal
trifluoroacetate, the iodine monochloride, and the solvent are
heated to a temperature from about 170.degree. C. to about
180.degree. C.
* * * * *